Organic Letters · 2021 · 29 citations · 40 references
Natural SciencesChemical EngineeringChemistryCatalysisElectrochemistryOrganic ChemistryCatalytic MechanismsCross-coupling ReactionsElectrochemical SynthesisHeterocycle SynthesisRedox CatalysisRedox-active MaterialsAromatic HeterocyclesCathode ProcessesElectrochemical C - N Bond FormationElectrochemical Coupling ReactionsFunctional Group ToleranceMild Reaction ConditionsNickel-catalyzed Cross-couplingPaired Electrolysis
We develop an electrochemical nickel-catalyzed aminomethylation of aryl bromides under mild conditions. The convergent paired electrolysis makes full use of anode and cathode processes, free of a terminal oxidant, a sacrificial anode, a metal reductant, and a prefunctionalized radical precursor. In addition, this method exhibits wide functional group tolerance (63 examples), including some sensitive substituents and aromatic heterocycles. This redox neutral cross coupling provides a more environmentally friendly and synthetic practical protocol for forging C(sp2)–C(sp3) bonds.
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Zhiwei Zuo, Derek T. Ahneman, Lingling Chu et al. · Science · 2014 · 1.6K citations · Full text
John C. Tellis, Christopher B. Kelly, David N. Primer et al. · Accounts of Chemical Research · 2016 · 687 citations · Full text